Acetic Anhydride → HCID 11380896, compound

HRID 495137Notes

Reaction equation

HRID 495137 reaction equation
FC(F)(F)C(O)=[O:4].[Cl:8][C:9]1[CH:10]=[CH:11][C:12]2[O:17][C:16](=[O:18])[CH:15]=[C:14]([O:19][CH2:20]CCNC)[C:13]=2[CH:25]=1.CC[N:28]([CH:32]([CH3:34])C)[CH:29]([CH3:31])C.C(OC(=O)C)(=O)C>C(Cl)Cl>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]2[O:17][C:16](=[O:18])[CH:15]=[C:14]([O:19][CH2:20][CH2:34][CH2:32][NH:28][C:29](=[O:4])[CH3:31])[C:13]=2[CH:25]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 86596924HCID 86596924, compound

Product 1

HCID 11380896HCID 11380896, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-chloro-4-(3-methylamino-propoxy)-1-benzopyran-2-one trifluoroacetic acid salt (0.272 mmol, 100 mg) is suspended in 3 mL of DCM. DIEA (0.544 mmol, 95 μL) is added followed by acetic anhydride (0.816 mmol, 77.1 EL). After stirring for 1 hr at ambient temperature, the reaction mix is concentrated in vacuo and purified by reversed-phase HPLC to afford the title compound (39.0 mg, 49%). 1H NMR (DMSO-d6, 300 MHz) δ 7.95 (1H, br t), 7.79 (1H, d, J=2.5 Hz), 7.72 (1H, dd, J=2.5, 8.75 Hz), 7.46 (1H, d, J=8.75 Hz), 5.95 (1H, s), 4.23 (2H, t, J=6 Hz), 3.24 (2H, q, J=6 Hz), 1.95 (2H, m, J=6.25 Hz), 1.80 (3H, s); MS (ESI, Pos.) calcd for C14H14ClNO4 m/z [M+H]=296.1, found 296.2.

Workup

  1. additionthe reaction mix
  2. concentrationis concentrated in vacuo
  3. custompurified by reversed-phase HPLC

Sources & evidence

ORD record
ord-3aedf8906ba44553b7981232a645c587
Source dataset
uspto-grants-2009_05
Patent number
US07538233B2

Reaction notes

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